Skip to Content
Merck
All Photos(3)

Key Documents

View All Documentation

T0642

Sigma-Aldrich

Tubercidin

from Streptomyces tubercidicus, ~95%

Synonym(s):

7-Deazaadenosine

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C11H14N4O4
CAS Number:
69-33-0
Molecular Weight:
266.25
Beilstein/REAXYS Number:
38498
EC Number:
200-703-4
MDL number:
MFCD00056012
UNSPSC Code:
51102829
PubChem Substance ID:
24899902
NACRES:
NA.85
Pricing and availability is not currently available.

biological source

Streptomyces tubercidicus

assay

~95%

form

powder

color

off-white

antibiotic activity spectrum

fungi
parasites
viruses

mode of action

DNA synthesis | interferes

SMILES string

O[C@H]1[C@@H](O)[C@H](N2C=CC3=C2N=CN=C3N)O[C@@H]1CO

InChI

1S/C11H14N4O4/c12-9-5-1-2-15(10(5)14-4-13-9)11-8(18)7(17)6(3-16)19-11/h1-2,4,6-8,11,16-18H,3H2,(H2,12,13,14)/t6-,7-,8-,11-/m1/s1

InChI key

HDZZVAMISRMYHH-KCGFPETGSA-N

Gene Information

rat ... Adora1(29290)

Looking for similar products? Visit Product Comparison Guide

General description

Chemical structure: nucleoside

Application

It is used to study tubercidin′s mechanism of toxicity, tubercidin resistance and is used as a selection agent. Tubercidin is used to study RNAi silencing[1]. It is used to study the role of transmethylation in chemotaxis of eukaryotic cells[2].

Biochem/physiol Actions

Toxic adenosine analog with antiviral, antitrypanosomal, and antifungal functions. Mode of action: Inhibits multiple metabolic processes, including RNA processing, nucleic acid synthesis, protein synthesis, and methylation of tRNA through intracellular incorporation into nucleic acids. Tubercidin acts as a plant antifungal, inhibits mammalian SAH hydrolase (SAHH), and blocks purine biosynthesis in Candida famata.
Tubercidin is a toxic adenosine analog with antiviral, antitrypanosomal, and antifungal functions. It inhibits multiple metabolic processes, including RNA processing, nucleic acid synthesis, protein synthesis, and methylation of tRNA through intracellular incorporation into nucleic acids. Tubercidin acts as a plant antifungal, inhibits mammalian SAH hydrolase (SAHH), and blocks purine biosynthesis in Candida famata. Tubercidin inhibits glycolysis in Trypanosoma brucei[1]. Tubercidin inhibits both chemotaxis and chemotaxis-dependent cell streaming of Dictyostelium, and chemotaxis of neutrophils at concentrations that have little effect on cell viability[2].

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H300

Hazard Classifications

Acute Tox. 2 Oral

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000276507
0000276507
067K2626
030H7255
010H72041

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 2

1 of 2

Tunicamycin from Streptomyces sp.

Sigma-Aldrich

T7765

Tunicamycin from Streptomyces sp.

Dexamethasone powder, BioReagent, suitable for cell culture, ≥97%

Sigma-Aldrich

D4902

Dexamethasone

Feng Sun et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 879(3-4), 285-290 (2011-01-05)
A sensitive and selective LC-MS/MS based bioanalytical method was developed and validated for the quantification of 3-deazaneplanocin A (DZNep), a novel epigenetic anti-tumor drug candidate, in Sprague-Dawley (SD) rat biosamples (plasma, urine, feces and tissue samples). The method comprises a
Laura Piel et al.
Frontiers in cellular and infection microbiology, 8, 325-325 (2018-10-05)
Leishmania biomarker discovery remains an important challenge that needs to be revisited in light of our increasing knowledge on parasite-specific biology, notably its genome instability. In the absence of classical transcriptional regulation in these early-branching eukaryotes, fluctuations in transcript abundance
Marco Singer et al.
Journal of the American Chemical Society, 132(24), 8372-8377 (2010-05-21)
Photochromic nucleosides were designed that combine the structural features and molecular recognition properties of nucleic acids with the light-sensitivity of diarylethenes. Target compounds 1a-c consist of a 7-deazaadenosine unit that is linked to a thiophene as the second aryl functionality
David B Olsen et al.
Antimicrobial agents and chemotherapy, 55(2), 937-939 (2010-12-01)
Efforts to develop novel, interferon-sparing therapies for treatment of chronic hepatitis C (HCV) infection are contingent on the ability of combination therapies consisting of direct antiviral inhibitors to achieve a sustained virologic response. This work demonstrates a proof of concept
Eiji Ohara et al.
Journal of hepatology, 54(5), 872-878 (2010-12-15)
The current treatment regimen for chronic hepatitis C virus (HCV) infection is peg-interferon plus ribavirin combination therapy. The majority of developing therapeutic strategies also contain peg-interferon with or without ribavirin. However, interferon is expensive and sometimes intolerable for some patients
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service